We were close friends, and I was interested, but one or the other of us had an SO for most of the time we knew each other. Finally we had synchronized breakups and started having more and more overtly sexual conversations. We were in her apartment drinking, and she stripped, stripped me naked and then despite telling me I had a gorgeous cock, decided we shouldn't fuck. We passed out cuddling naked with each other, and when I woke up, she was masturbating. I flipped her over and started masturbating too, which got her really rev'd up, she came, I came on her. Still didn't want to fuck, but ok.
Couple of weeks later we were drunk again, she wanted to fuck, but we didn't have a condom, so we started masturbated together, and finished each other off with oral. A few days later, we're hanging out and drinking again, and she asks me if I like anal. I say yes, and she says she's never managed it but always wanted to. We start talking and agree to try anal together. We get butt plugs, an enema kit and lots of lube, and spend an afternoon playing with her ass before finally I managed to get it in. She played with her clit while I fucked her ass, and she came several times.
We showered, and I asked if she wanted a round two of normal sex and she said, "I still don't think we should sleep together."
What the fuck. It gets better though.
For the next week or so, we had anal almost daily, and one day I fucked her ass three times. No PIV sex, no blow jobs, just anal. Then she announced that she finally had the confidence to try anal with other guys, and she was going to make a move on this guy she liked. I basically said, "We've been fucking all week, I know you like me, so why aren't we more than just butt-fuck buddies?"
Her answer, "You're a good friend, you're hot and I totally want to fuck you, and I love when you fuck my butt, but I feel like we'd be a lousy couple." After hearing that answer, I realized she was right, because that's just plain messed up in the head.
We did end up fucking numerous times over the next few years, including plenty of plain old PIV, but we never dated, and freely saw other people. She would occasionally get jealous of my girlfriends, but respected my relationships and never made a move or tried anything when I was with someone, and I did the same. She drunkenly told me "I love you" dozens of times, and would occasionally talk about "our kids", but would never date me. I always had feelings, but we did work well as friends / fuck buddies and maybe she was right, we weren't couple material. She was cool, but messed up.